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Identification
NameOxamic Acid
Accession NumberDB03940  (EXPT02460)
TypeSmall Molecule
GroupsExperimental
Description

Amino-substituted glyoxylic acid derivative. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIQU60N5OPLG
CAS number471-47-6
WeightAverage: 89.0501
Monoisotopic: 89.011292967
Chemical FormulaC2H3NO3
InChI KeyInChIKey=SOWBFZRMHSNYGE-UHFFFAOYSA-N
InChI
InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6)
IUPAC Name
carbamoylformic acid
SMILES
NC(=O)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Primary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8047
Blood Brain Barrier+0.9244
Caco-2 permeable-0.8392
P-glycoprotein substrateNon-substrate0.8645
P-glycoprotein inhibitor INon-inhibitor0.9828
P-glycoprotein inhibitor IINon-inhibitor0.99
Renal organic cation transporterNon-inhibitor0.9803
CYP450 2C9 substrateNon-substrate0.8713
CYP450 2D6 substrateNon-substrate0.8657
CYP450 3A4 substrateNon-substrate0.7818
CYP450 1A2 substrateNon-inhibitor0.9675
CYP450 2C9 inhibitorNon-inhibitor0.9667
CYP450 2D6 inhibitorNon-inhibitor0.9565
CYP450 2C19 inhibitorNon-inhibitor0.9694
CYP450 3A4 inhibitorNon-inhibitor0.9764
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9972
Ames testNon AMES toxic0.8384
CarcinogenicityNon-carcinogens0.781
BiodegradationReady biodegradable0.8507
Rat acute toxicity1.0426 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.999
hERG inhibition (predictor II)Non-inhibitor0.9862
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point210 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility108.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.26 m3·mol-1ChemAxon
Polarizability6.65 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-01b9-4900000000-a5c7d6900f929f7102bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-68b3969cef554dca4e23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-785f3a8aab8f2ac5f598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4f5256271ccf6a7d0e19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-1348db048c59f511f37fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-7ed633dbb477c19204b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f3903e56dedef1549964View in MoNA
References
Synthesis Reference

Shinsuke Shirakawa, Kazunori Kanda, Mitsuo Yamada, Kei Aoki, Satoshi Urano, Nobuaki Tomita, “Compound containing an oxamic acid group, a process for producing the compound, and a resin composition containing the compound.” U.S. Patent US5663262, issued August, 1987.

US5663262
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Plasmodium falciparum (isolate CDC / Honduras)
Pharmacological action
unknown
General Function:
L-lactate dehydrogenase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q27743
Molecular Weight:
34107.505 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
unknown
General Function:
L-malate dehydrogenase activity
Specific Function:
Not Available
Gene Name:
ldh
Uniprot ID:
P16115
Molecular Weight:
34994.11 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nad binding
Specific Function:
Not Available
Gene Name:
LDHA
Uniprot ID:
P00338
Molecular Weight:
36688.465 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nad binding
Specific Function:
Not Available
Gene Name:
LDHB
Uniprot ID:
P07195
Molecular Weight:
36638.225 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Formate c-acetyltransferase activity
Specific Function:
Not Available
Gene Name:
pflB
Uniprot ID:
P09373
Molecular Weight:
85356.555 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Lactobacillus helveticus
Pharmacological action
unknown
General Function:
Nad binding
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P30901
Molecular Weight:
37778.94 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Symporter activity
Specific Function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:
SLC16A3
Uniprot ID:
O15427
Molecular Weight:
49468.9 Da
References
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [PubMed:11101640 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23